Tert-Butylamine → HCID 86616350, compound

HRID 898836Notes

Reaction equation

HRID 898836 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]([NH2:11])([CH3:10])([CH3:9])[CH3:8].S(=O)(=O)=O.[C:16](OC(=O)C)(=[O:18])[CH3:17]>C1(C)C=CC=CC=1>[C:16]([O:1][CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:11][C:7]([CH3:10])([CH3:9])[CH3:8])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 6385Tert-Butylamine2×HCID 7918Acetic AnhydrideHCID 24682Sulfur trioxide2×HCID 312751,4-Dioxane3×

Product 1

HCID 86616350HCID 86616350, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
22.5 °C

Procedure

The reaction time for cleavage of 1,4-dioxane was 2 hours at 120-125° C. and for animation with t-butyl amine was 30 minutes at 140-145° C. A 50 mL one-necked flask was charged with 1,4-dioxane (12 mL, 12.4 g, 140 mmol) under a nitrogen atmosphere. Then sulfur trioxide (2.6 g, 32.5 mmol, polymer) was added followed by addition of acetic anhydride (6.2 mL, 6.6 g, 65 mmol) at 10-15° C. The reaction mixture was stirred at 20-25° C. for 15 minutes to dissolve sulfur trioxide (time may very depending on size of pieces of SO3). The reaction mixture was then transferred to a sealed tube and heated at 120-125° C. for 2 hours. After cooling, the mixture was transferred to one neck 100 mL flask and concentrated under vacuum (1 mm) at 60-65° C. 1,4-dioxane (5 mL, 5.2 g, 58.7 mmol) and tert-butylamine (20 mL, 14 g, 190 mmol) were added to the residue with stirring and cooling. The mixture was transferred to a sealed tube and heated at 140-145° C. for 30 minutes. Then the reaction mixture was cooled to room temperature. Toluene (40 mL) was added with stirring and the mixture was filtered under vacuum. The precipitate was washed with toluene (10 mL) and then concentrated under vacuum to 25-30 mL. The toluene layer was separated from the insoluble bottom oil and the solvent was removed under vacuum to give crude product 2-(2-tert-butylaminoethoxy)ethyl acetate (3.8 g, 20 mmol, approximately 62.5%).

Workup

  1. customThe reaction mixture was then transferred to a sealed tube
  2. temperatureheated at 120-125° C. for 2 hours
  3. temperatureAfter cooling
  4. concentrationconcentrated under vacuum (1 mm) at 60-65° C
  5. stirringwith stirring
  6. temperaturecooling
  7. customThe mixture was transferred to a sealed tube
  8. temperatureheated at 140-145° C. for 30 minutes
  9. temperatureThen the reaction mixture was cooled to room temperature
  10. stirringwith stirring
  11. filtrationthe mixture was filtered under vacuum
  12. washThe precipitate was washed with toluene (10 mL)
  13. concentrationconcentrated under vacuum to 25-30 mL
  14. customThe toluene layer was separated from the insoluble bottom oil
  15. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-5b71e81bdd204a82a4dd1b770c1d7497
Source dataset
uspto-grants-2008_04
Patent number
US07351865B2

Reaction notes

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